I don't have as much sailing experience as the poster, but I did have my CSA basic keel boat certification that I got hear in Canada.

I did a live aboard sailing course last ay with a friend (search fair wind sailing and you should find my review). Although I would not recommend this operator I would recommend taking a live aboard course. It's a great introduction to the islands and will give you the confidence to challenge them on your own next time. There are a few draw backs with going with a live aboard sailing course, you may be teamed up with 2 or 4 more people (this could make or break the experience), the days are long and there is a lot of material to cram in. My buddy and I did extensive prep and read/memorized all the material before going on the course. The couple that we were sailing with did not and they struggled! Started getting frustrating towards the end of the course when we were trying to refine our sailing skills and they were still struggling with basic sailing terms and maneuvers (e.g. "Prepare to tack!"....response, "what do I do again?" <img src="http://www.traveltalkonline.com/forums/images/graemlins/duh.gif" alt="" />)

My buddy and I and respective wives are chartering in May and feel confident that we can handle a 40'...go slow and reef early! We are still mulling over getting a captain for a day to refresh our skills. We'll see.

Anyway, all that to suggest that if you have the money you may want to consider chartering a boat and getting a captain to take you through the certification. Good luck!